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Facile access to structurally diverse antimalarial indoles using a one‐pot A3 coupling and domino cyclization approach

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dc.contributor.authorSilva, Gustavo Da
dc.contributor.authorLuz, André F. S.
dc.contributor.authorDuarte, Denise
dc.contributor.authorFontinha, Diana
dc.contributor.authorSilva, Vera L. M.
dc.contributor.authorAlmeida Paz, Filipe A.
dc.contributor.authorMadureira, Ana Margarida
dc.contributor.authorSimões, Sandra
dc.contributor.authorPrudêncio, Miguel
dc.contributor.authorNogueira, Fátima
dc.contributor.authorSilva, Artur M. S.
dc.contributor.authorMoreira, Rui
dc.date.accessioned2023-09-12T13:16:47Z
dc.date.available2023-09-12T13:16:47Z
dc.date.issued2023
dc.description© 2023 Wiley-VCH GmbHpt_PT
dc.description.abstractA multistep and diversity-oriented synthetic route aiming at the A3 coupling/domino cyclization of o-ethynyl anilines, aldehydes and s-amines is described. The preparation of the corresponding precursors included a series of transformations, such as haloperoxidation and Sonogashira cross-coupling reactions, amine protection, desilylation and amine reduction. Some products of the multicomponent reaction underwent further detosylation and Suzuki coupling. The resulting library of structurally diverse compounds was evaluated against blood and liver stage malaria parasites, which revealed a promising lead with sub-micromolar activity against intra-erythrocytic forms of Plasmodium falciparum. The results from this hit-to-lead optimization are hereby reported for the first time.pt_PT
dc.description.sponsorshipThe authors acknowledge the financial support provided by Fundação para a Ciência e a Tecnologia (FCT Portugal) through the PhD grant research project SFRH/BD/103412/2014 and projects PTDC/MED-QUI/30021/2017, PTDC/MED-CAR/31322/2017 and PTDC/SAU-TOX/32515/2017, and the research unit GHTM (UID/Multi/04413/2013 and GHTM-UID/04413/2020).pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationChemMedChem. 2023 Sep 1;18(17):e202300264pt_PT
dc.identifier.doi10.1002/cmdc.202300264pt_PT
dc.identifier.eissn1860-7187
dc.identifier.issn1860-7179
dc.identifier.urihttp://hdl.handle.net/10451/59230
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherWileypt_PT
dc.relationPTDC/MED-CAR/31322/2017pt_PT
dc.relationDiscovery of novel Quinolone-based antimalarials using the Winterfeldt chemistry
dc.relationGHTM-UID/04413/2020pt_PT
dc.relationNew Psychoactive Substances - A Platform for Risk Assessment of Teens Brain Exposure
dc.relationGlobal Health and Tropical Medicine
dc.relation.publisherversionhttps://chemistry-europe.onlinelibrary.wiley.com/journal/18607187pt_PT
dc.subjectA3 couplingpt_PT
dc.subjectAntimalarialspt_PT
dc.subjectIndolespt_PT
dc.subjectMulticomponent reactionspt_PT
dc.subjectOne-pot synthesispt_PT
dc.titleFacile access to structurally diverse antimalarial indoles using a one‐pot A3 coupling and domino cyclization approachpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleDiscovery of novel Quinolone-based antimalarials using the Winterfeldt chemistry
oaire.awardTitleNew Psychoactive Substances - A Platform for Risk Assessment of Teens Brain Exposure
oaire.awardTitleGlobal Health and Tropical Medicine
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/OE/SFRH%2FBD%2F103412%2F2014/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FMED-QUI%2F30021%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FSAU-TOX%2F32515%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FMulti%2F04413%2F2013/PT
oaire.citation.issue17pt_PT
oaire.citation.titleChemMedChempt_PT
oaire.citation.volume18pt_PT
oaire.fundingStreamOE
oaire.fundingStream3599-PPCDT
oaire.fundingStream3599-PPCDT
oaire.fundingStream6817 - DCRRNI ID
person.familyNameda Silva
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person.givenNameGustavo
person.givenNameAndré
person.givenNameDiana
person.givenNameAna Margarida
person.givenNameSandra
person.givenNameMiguel
person.givenNameRui
person.identifierC-2614-2014
person.identifierhttps://scholar.google.pt/citations?user=zduN6wsAAAAJ&hl=pt-PT&oi=ao
person.identifierG-7485-2011
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person.identifier.ciencia-id5511-16ED-48E0
person.identifier.ciencia-id8B11-E8C0-DFD0
person.identifier.orcid0000-0002-1805-5662
person.identifier.orcid0000-0003-3611-4598
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person.identifier.orcid0000-0002-5685-1790
person.identifier.orcid0000-0003-1746-6029
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person.identifier.ridM-7564-2013
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project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
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project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsrestrictedAccesspt_PT
rcaap.typearticlept_PT
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